Apartments for Rent in Virginia Heights, Winter Park, FL

Unbeatable Location! Don't miss this very rare and exquisite 3 bedroom, 2.5 bath, two-story Executive-Style condo in Winter Park-ideally located just around the corner from N. Orange Avenue, Park Avenue and Rollins College. Nestled in a prime, tucked-away setting, this home has been extensively remodeled with all new plumbing, electrical, duct work, flooring, appliances, and a natural gas line. In addition, two newer HVAC systems were installed in November 2022, offering modern efficiency and reliability. The gated front courtyard, thoughtfully designed by a landscape arc

Property Status: Active Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the vibrant Winter Park area has to accord. Don't miss the opportunity to make this your new home! Office Phone: (844) 239-2663 Copyright © 2026 Stellar MLS. All r

Property Status: Active Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College. Office Phone: (407) 406-5300 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be indep

Available immediately Located at 362 S Pennsylvania Ave (3rd floor) in the highly desirable Hannibal Square area of Winter Park, this spacious 2-bedroom, 2-bathroom apartment puts you right in one of the most walkable and vibrant neighborhoods in Central Florida. Steps away from the restaurants, cafés, and boutique shops around Hannibal Square, and only a short walk to Park Avenue, the Winter Park Farmers Market, the SunRail station, parks, and local cultural spots. The neighborhood is known for its historic charm, art scene, and great dining options. Apartment details

Property Status: Active Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & open layout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining or casual family meals. Granite countertops, stainless steel appliances, self-closing cabinets, and stylish finishes that reflect quality and fresh design. Newer insulated windows including large sliding do

**Move-in ready starting June 1st!! | Schedule your tour today! ** Welcome to your new home! This charming 4 bed, 2 bath home in beautiful Winter Park is waiting for you to make it yours. The beautiful hardwood floors throughout the house give it a cozy and inviting feel. Enjoy the sunshine in the sunroom, or step outside and relax in the spacious yard with a fence. You'll love the convenience of the great location - just minutes away from shops, restaurants, Rollins College, and more! Whether you're a Rollins student looking for the perfect home away from home or just lo

Rare opportunity to rent a spacious 5-bedroom, 3-bath home in Orlando’s vibrant Mills 50 District. This two-story home offers plenty of space and character, featuring a decorative fireplace, formal living room, 2-car garage, screened porch, and a fully fenced yard. Lawn care is included, making maintenance easy. The home is available immediately. Pets will be considered on a case-by-case basis with a pet fee and monthly pet rent. Residents enjoy an unbeatable location directly across from Lake Estelle, with easy access to some of Orlando’s favorite parks and attractions.

Property Status: Active Stylish, move-in ready townhome in the heart of Baldwin Park! This well-appointed two-story home offers three bedrooms, two and a half baths, and 1,632 SF of thoughtfully designed living space. The remodeled kitchen is a true showstopper — featuring modern finishes and sleek black stainless steel appliances, it opens seamlessly to a generous living room with warm hardwood floors throughout. Upstairs, the spacious primary suite includes an en suite bath with double sink vanity and a walk-in closet, while two additional guest bedrooms share a well-app

Property Status: Active Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix, Trader Joe's, Regal Movie Theater, and a variety of restaurants and bars. Join this vibrant community and make this beautiful condo your new investment property

Property Status: Active Occupying the entire second floor of a landmark 1925 brick building in the heart of Winter Park, this fully reimagined residence offers a rare opportunity to lease a true designer 3 bedroom, 3 bathroom loft just two blocks from Park Avenue. The open concept interior features high ceilings, abundant natural light from skylights and brand new windows, and a refined industrial aesthetic anchored by hardwood flooring and sleek quartz countertops. A custom architectural lighting package with sculptural glass pendants and vertical LED sconces adds a disti

Property Status: Active What a wonderful garage apartment that comes with ALL Utilities including: electric, water, sewer, wifi, and cable! This one bedroom apartment is located off of Blue Jacket Park giving you access to everything that is wonderful about Baldwin Park. Inside you will find neutral wall color, wood flooring throughout, a number of windows providing lots of natural light. Most windows have wood shutters. The kitchen is well appointed with stainless appliances and there is a full size stackable washer and dryer inside this home. In addition to the rent

Property Status: Active This is a unique opportunity to live in this glamorous, impeccably maintained 3 bedrooms, 2.5 baths in the heart of Winter Park (Unfurnished). This beautiful home features formal living and dining rooms that open to the impressive gourmet kitchen fitted with wood cabinetry, stainless steel appliances, granite countertops, a breakfast bar, there is also room for a breakfast nook. Through the kitchen, French doors lead you to your own secluded large patio retreat. A spacious master bedroom upstairs features a large ensuite with two separate vanities,

Welcome to your future home in the charming district of Winter Park, FL! This inviting property offers a warm atmosphere perfect for relaxation and convenience, surrounded by a vibrant community. This residence boasts spacious living equipped with essential comforts. With ample bedrooms and bathrooms, it accommodates various lifestyles. You'll appreciate the central heating and cooling systems, alongside the refreshing ceiling fans, ensuring your comfort year-round. Nestled in a prime location, you'll be just a short walk away from delightful restaurants and beautiful ou

Welcome to this stunning townhome in the heart of Winter Park, built by award-winning Osprey Custom Home Builders. This residence combines timeless design, coastal aesthetic, certified greb construction, energy efficiency, and modern smart-home conveniences. Featuring 3 bedrooms, 2.5 baths, and an open-concept layout, the home is filled with designer finishes and thoughtful details throughout. The first floor offers inviting living and dining areas with plank-style tile floors, surround sound speakers, and high ceilings. The gourmet kitchen is equipped with maple cabinetry

Property Status: Active Exceptional Lakefront Living in the Heart of Winter Park Welcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle. Property Highlights: Situated on an oversized lot with coveted Lake Killarney frontage and a private boathouse, this elegant two-story home showcases engineered wood flooring throughout and an open-concept design flooded with natural light. Soa

Property Status: Pending PRICE REDUCED | $3,550/Month | Baldwin Park Townhome | Available Now Your next chapter starts here. This beautifully appointed Baldwin Park townhome just got more accessible — with a reduced rent, it's the right home at the right time. Spanning 1,897 square feet, this residence offers something truly hard to find: two full primary suites, each with its own en suite bath and walk-in closet. Whether you're sharing with a roommate, accommodating family, or simply wanting a dedicated home office with its own retreat, this layout delivers. The main leve

Coming soon, Enjoy Winter Park's most desirable location! One block from Park Avenue/Central Park. Spacious, bright and all on the second floor with private elevator access and secured underground parking. Luxury living all on ONE floor! This beautiful home offers a short walk to everything Winter Park has to offer. Natural light fills the central courtyard which features an iron water fountain. Private pool with heated spa and outdoor grilling and entertaining area are a perfect spot to entertain guests. Interior features include fireplaces in living room, 2 South West fa

Winter Park at your door step! This is a second floor 2 bedroom unit, in secured building. Large open backyard with rear balcony and patio space and plenty of parking. Unit has full kitchen, and washer/dryer in unit! Two full bedrooms both with walk-in closets and a full bath. Living room is large open/bright. Only a few blocks walk to Orlando Ave with all its shopping, Publix and restaurants. Easy access to downtown Winter Park or Downtown Orlando without the need of I-4. Available today no HOA

Nestled in a tranquil street, this house is steps away from Lake Killarney, ideal for kayaking or simply enjoying picturesque water views Immerse yourself in the heart of Winter Park and enjoy the convenience of the nearby Winter Park Village, Trader Joe's, Whole Foods, a curated selection of trendy restaurants, upscale cafés and boutique shopping 5 minutes to Rollins College and downtown Winter Park – a hub for arts, culture, and fine dining Less than a minute’s drive to I-4, ideal for commuters Walking distance to Tennis/Pickleball Court, Coffee shops and restaurants Top

Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99). HOAs may also charge mandatory application and amenity fees, where applicable, which must be paid directly to the HOA. For a comprehensive overview of all potentia

The advertised rate of $1,302/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 1, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be higher if billed in multiple payments. Welcome to a calm and comfortable Orlando retreat in a tiny home in College Park, perfectly placed for exploring the city while enjoying a space